


Sam Winchester's Guide to Living With Dean Winchester (For Angels)

by Smidgenofthesea



Category: Supernatural
Genre: Castiel & Sam Winchester Friendship, Dean Winchester Has a Cowboy Kink, M/M, Other Additional Tags to Be Added, Sam Winchester Ships Castiel/Dean Winchester, Sam Winchester is a Saint, porn will come later
Language: English
Status: In-Progress
Published: 2018-06-22
Updated: 2018-08-05
Packaged: 2019-05-26 19:35:18
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,512
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15007871
Author URL: https://archiveofourown.org/users/Smidgenofthesea/pseuds/Smidgenofthesea
Summary: Sam only wants to help his brother and their angel have the healthiest relationship possible. If the only way to do that it to write a list of things that will help Cas deal with Dean, then so be it.Or, The One Where Sam Meddles (Like, A Lot)





	1. Sam Just Wants to Help

**Author's Note:**

> Okay, so this is really my first multi chapter story, that's not straight up porn. (there will be porn later, almost certainly)  
> My goal is to write a chapter/stand alone story for each bullet point on Sam's list. The list as it stands is not complete. I'll keep adding to it, and if you think of something that Sam should tell Cas that would make a fun story, let me know!  
> I have absolutely no idea how long this will be, but I do kind of have an ending in mind. Ish.
> 
> Completely unbeta'd, concrit and typo-pointing-out welcome!

“Sam Winchester’s Guide to Living With Dean Winchester.”

Sam didn’t set out to write a cheat sheet for Cas, but who better to advise the angel than the one person who’d known Dean for 30+ years? And really, Cas was already playing with a handicap, having never been in a human relationship before. And when that human was Dean Winchester, well. The angel could use all the help he could get. So it was pure altruism that lead him to open a Google Drive document and start to catalog his brother’s many...eccentricities. 

Sam was pretty damn ecstatic when Dean and Castiel finally got their shit together and admitted they loved each other. He was really looking forward to a bunker unburdened by unresolved sexual tension thick enough that he could have screamed.  
At least, that’s what he was hoping for. In reality it was more like a week and a half of peace and quiet (if you ignored the rhythmic thumping and occasional yelps from Dean’s room, which he had decades of experience doing), interrupted by their first lover’s spat.  
Being the third wheel wedged between the all-time champions of the Eye Fucking Olympics was bad enough. But the icy silence and childish behavior was even worse. Passive aggressive jabs flew back and forth. Books were thumped down dramatically. Doors were slammed. Footsteps stomped up and down the stairs. Sam was concerned for the structural integrity of the bunker, as well as his own sanity. So he did what came naturally. He meddled.

“Dean. What the hell. Why are you being such a bitch?” Sam asked when he’d cornered his brother in the library.  
“Sammy, leave it. It’s Nunya.”  
“What?”  
“Nunya goddamn business, now leamme alone!” Dean barked. He tried to get past his little brother, but Sam stood his ground.  
“It becomes my business when it affects our ability to hunt together. You and Cas haven’t spoken to each other in a week. Hell, you won’t even LOOK at him. Pull your shit together.”  
“Good talk, Sam. I feel better already. Now get outta my way.”  
Sam sighed heavily as Dean shouldered his way past and down the hallway to his room.  


Well, if his brother wouldn’t see reason, maybe the angel would.  
Sam knocked on the door of the room that was nominally Cas’s. Lately he’d been living in Dean’s room, but when Sam knocked, he heard a quiet “Come in.”  
Cas looked like shit, his clothes were wrinkled and heavy bags hung below his eyes. The angel was sitting listlessly on a bed that clearly hadn’t been slept in.  
“Hello Sam.”  
“Heya Cas. How’s it going?”  
Cas rolled his eyes and heaved a Sam-worthy sigh. “Your brother is even more frustrating as a romantic partner than as a friend. I had not thought it was possible for him to infuriate me more than he already did. I was clearly mistaken.”  
Sam tried not to laugh too hard at that, but nodded.  
“Yeah, it probably doesn’t help that his only real relationships ended pretty terribly. He doesn’t really know what he’s doing, Cas.”  
“Neither do I” Cas retorted.  
Sam inclined his head in a gesture of agreement.  
“What did you guys argue about?”  
Sam wouldn’t have thought it possible, but Cas’s cheeks tinged with pink when he responded.  
“I was too...eager...to commence certain activities and Dean was frustrated that I wouldn’t let him ‘take some goddamn time to open me up so he didn’t hurt me’ and when I reminded him that I was much less fragile than a human; and unlike him could handle even the most vigorous anal intercourse, he seemed to get angry. After that he was determined to pick a fight.”  
_Oh, god, oh the air quotes_. Sam thought longingly of a world where he lived in peace and had absolutely no information about his brother’s sex life. Ugh.  
_Well, it’s too late for the last bit, but I might still be able to get some peace around here._  
“Cas, I think talking about you being an angel scares the hell out of him. Honestly, I think he’s still convinced you’re going to pack up and leave for Heaven again. You two might want to deal with that. And uh, maybe apologize for comparing your angelic ass to his?”  
Cas made a sound of pure frustration.  
“I would if he would talk to me! I’ve tried, and every time I bring it up, he walks out of the room! I just need him to stay put for two minutes.” He picked mournfully at the ratty bedspread.  
“How do I get him to listen?”  
Sam took a deep breath and prepared to meddle in his brother’s love life- _for his own damn good_ -and said firmly,  
“Cowboy boots.”  
“Excuse me?”  
“Dean has this thing. About cowboys. And if you show up at his door in cowboy boots and a hat maybe”- _oh this is getting away from me shit shit shit_ \- Sam gulped and plowed on “maybe his brain will stall long enough for you to get him to listen.”  
Cas didn’t look convinced. “Maybe?” “Probably. Honestly, if you dress up as a cowboy, you can probably get him to do anything you want.” _Does this count as betraying Dean? I mean, he’s gonna end up getting some epic sex, and all I get is more trauma._ A mischievous smile played at Cas’s lips. He stopped tugging on the lint balls in the blanket, and his eyes seemed to focus in the distance, as if he were already planning something.  
“Thank you, Sam. I think I will take your advice.” 

When Dean asked later if Sam knew where Cas had gone, he shrugged. He didn’t actually know for sure that Cas was at the Western Wear outlet in town. Maybe he just went for a drive.  
Dean spent the rest of the afternoon in his room, Metallica blaring.  
Cas got back to the bunker already wearing his cowboy duds. Sam looked up from the document he was working on in the war room. Cas smiled and spread his hands, showing off the outfit and silently asking Sam’s opinion. The deep blue plaid complimented his uncannily blue eyes, and the cut showed off his strong shoulders. The weathered jeans were tight enough to hug his thighs, and a big silver belt buckle brought it all together. The boots were plain black leather, but the silver spurs- _oh my god, Dean is going to have a heart attack_ -jingled softly with every step. The final piece, the black cowboy hat, had a leather band with silver cabochons set around the crown. Cas was holding it in his hands, turning it nervously as he awaited Sam’s opinion.

“You look great, Cas. Go get ‘em.” Sam waited at the table until he heard Cas knock on Dean’s door. He heard Dean’s voice, but couldn’t understand the words. The slam of the door, and the moans that followed, were easy to translate. He put headphones on and continued with his writing:  


“Sam Winchester’s Guide to Living With Dean Winchester”

  * He can’t resist cowboys. Actually, he’s got a thing for doctors too. And maybe wrestlers.  



  * He always, always throws scissors.  



  * If he’s snoring, get him to lie approximately ¾ on his front, then tilt his head back a bit until he stops-use CAUTION when waking him. Or don’t, you’re an angel, anything under his pillow is unlikely to hurt you.  



  * Apologize with bacon. If that doesn’t work, apologize with bacon and cowboy boots.  



  * He’s kind of a neat freak.  



  * Dean says ‘I love you’ with food.




	2. When He Sounds Like a Duck Gargling Cement, or, How to Stop Dean Snoring

**Summary for the Chapter:**

> Dean snores. Cas suffers. Sam intercedes. So much fluff.

**Notes for the Chapter:**

> Pure tooth-rotting fluff and characterization. No porn. That's coming though, no worries. I don't know if anyone's reading this, but if so: I'm really sorry it took so long to update. I expect chapters to come in starts and fits, so please forgive the lack of posting schedule.
> 
> No beta, rough editing. If anyone feels like chiming in with concrit, feel free!

Cas loved watching over Dean while he slept.  
With his powers restored, he didn’t need to sleep, but it was still enjoyable to stretch out in bed at night. He loved the quiet of the bunker. It was the best time to read without being interrupted. Cas kept a stack of books next to his side of the bed which he was constantly refreshing. He loved being there to protect his Dean, even if only from bad dreams.

_Remember how much you love him_ Cas thought to himself. _You don’t actually want to murder him._ But as Dean’s snoring rose another decibel, murder was outweighing love.  
_I didn’t know humans could make those sounds. It’s like a demon-possessed pig suffering an allergy attack._  


The sound he could handle. It was loud, yes, but he wasn’t trying to fall asleep. He was just trying to concentrate on the paragraph which he had, at this point, read 5 times without absorbing. It was the staccato: The unholy noise started, Cas resigned himself to his fate and redoubled his concentration on the words in front of him. Then sudden silence. He held his breath. The snoring would start again, of course it would, _but when??_ Every second of silence, which should have been a reprieve, was torture. He could feel his shoulders creeping up around his ears. 

_Smothering with a pillow_ he considered, _would be a far more humane death than any of the others he’s suffered._  
He could, of course, simply leave the room and read elsewhere. But Sam and Dean had introduced Cas to the concept of comfy, and immediately regretted it. Prying Cas from a comfy position was more of a challenge than killing a Wendigo armed only with a Bic. Cas was comfortable, tucked in to his warm bed, under the soft blankets, on the mattress that remembered him, with his fuzzy bee socks and his threadbare Led Zeppelin t shirt, and the man he loved who he was going to smite to smithereens in about 5 more minutes. Cas heaved a weary sigh, pulled the covers back, and reluctantly got out of bed. In deference to the fact that he did actually love Dean, he did it quietly. However tempting it was to “accidentally” nudge the man on his way out, Cas took the high road. He recalled a time when he would have exploded people for less. Personal growth. 

He slipped out the door and headed towards the library. The bunker was utterly silent except for the soft shush of his feet. Cas expected the library to be dark, but a soft light warmed the room.  
Sam sat with his chin resting in his palm, elbow propped on the table, engrossed in the book laid out in front of him.  
“Sam. What are you doing awake?” Sam jerked at the intruding voice, then turned a soft smile on Cas.  
“Still think we should put a bell on you, dude. Couldn’t sleep, thought I might as well get some research done.”  
“Nightmares?”   
Sam nodded. “They’re getting better. It only happens every couple weeks now.”  
Cas pursed his lips. “I am so, so sorry.”   
Sam gave him a genuine, if tired smile.  
“I know you are. You know I forgave you a long time ago, right?”  
Cas dropped heavily into a chair. “I know. I will never understand humans.” Sam chuckled.  
“We do contain multitudes. Speaking of which, why aren’t you in creepy watching-Dean-sleep mode? You finally get tired of counting his freckles?” 

A deep blush rose up Cas’s neck, all the way to his hairline. “I regret ever saying that, and Dean assures me that anything said under the influence of tequila is inadmissible and should not be held against me. But no, I’m not bored. Rather the opposite.”  
Sam’s forehead wrinkled in confusion. “Is this a sex thing? If it’s a sex thing I don’t wanna know.”  
“It’s not a sex thing. Dean snores. I can’t concentrate on anything when I’m waiting for the next assault on my ear drums.”  
Sam and Cas were both surprised by the laugh that rose up out of Sam’s mouth. “Oh man. It’s been a long time since I had to listen to that. Bobby used to threaten to make him sleep outside in one of the junkers.” Sam ducked his head, savoring the memory, then looked up to meet Cas’s eyes.  
“You know he only sleeps that deep when he feels safe, right?” Cas shook his head, unsure of what to say.  
“Most of the time, when we were growing up, in and out of hotels, he slept light. Like, the tiniest noise and he’d be on his feet with a pistol in his hand. Hell, sometimes he didn’t even bother to undress. Just pass out for a few hours on top of the blankets.” Cas nodded, remembering the times he had come to check on Dean and found him in that exact position.  
“The few places he felt truly safe, the rare times when we could afford to relax, he’d snore loud enough to shake the house down. He feels safe with you.”  
Cas felt something thrum in his chest, a warmth spreading outward. “Thank you, Sam. I think...I think I’ll head back to bed. In case he wakes up in the night.” Sam nodded, breaking into a yawn. “Maybe you should try to get more sleep too.”  
Sam shook his shaggy head. “Nah, I’m not gonna get anymore sleep tonight. I’ll just get more nightmares. Besides, Eileen should be awake in a couple hours. I’ll skype her when she’s up.”  
Cas gave a small smile. “I’m glad you have someone to talk to. Please tell her hello for me. And now I’ll just head back to my date with a congested hippopotamus.”  
Cas turned and started back to the bedroom. “Hey, Cas.” Sam called after him. Cas stopped and turned.  
“Roll him like ¾ on his side. Tilt his head back.” Sam demonstrated, lifting his chin up. “That’s on the list.” Cas favored him with a real smile. “Thank you. I’ll have to reread it. Goodnight, Sam.” 

When he slipped back into their room, Dean was once again shoving logs through a woodchipper. _Turn him ¾ on his side._ Cas gently rolled Dean over. The awful noise lost several decibels. _I really must thank Sam. A fruit basket, perhaps. That’s standard, I believe._ Cas crawled into his side of the bed and settled in with his book propped on his chest. The snoring had lost most of its demonic pitch.  
Cas was relaxing into a pleasant drowse when Dean rolled against his side. His arm flopped across Cas’s waist with the weight of a ship docking at its home port. His head rested on Cas’s chest. _I’ve been colonized_ he thought as Dean mumbled and pushed his face into Cas’s chest like a kitten.  
Dean gave a contented hum and then was silent. The snoring stopped completely.  
Cas found himself grinning at the ceiling, pride and love swelling in his chest. If Dean needed Cas to be his human pillow, he would simply have to endure. Dean’s warmth melted into his side. Cas turned his head and push his nose into Dean’s hair, inhaling that unique mix of scents that had no description beyond “Dean.” Cas closed his eyes and let himself drift. The man he loved was safe by his side, he was warm and cozy, and all was right with the world. 


End file.
